?url_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Adc&rft.relation=http%3A%2F%2Fd-scholarship-dev.library.pitt.edu%2F7773%2F&rft.title=Synthesis+of+Pentafluorosulfanyl+Analogs+of+Mefloquine&rft.creator=Mo%2C+Tingting&rft.description=The+pentafluorosulfanyl+(SF5)+group+is+of+increasing+interest+as+a+functional+group+in+pharmaceutical+and+agrochemical+research%2C+and+was+recently+labeled+as+the+%22substituent+of+the+future%22.+It+imparts+unique+properties+to+organic+compounds+and+enhances+their+biological+activities+because+of+its+high+electronegativity%2C+substantial+steric+effect%2C+significant+hydrophobicity+and+high+chemical+resistance.+To+improve+the+activity+and+alleviate+the+neurotoxicity+of+the+anti-malarial+drug+Mefloquine%2C+we+introduced+the+SF5+group+into+the+quinoline+methanolamine+scaffold+in+place+of+the+trifluoromethyl+(CF3)+group.+Three+novel+mefloquine+analogs+were+synthesized+in+high+yields+from+simple+phenyl+SF5+building+blocks+through+short+synthetic+routes.+Two+analogs+were+found+to+have+improved+activity+and+selectivity+against+malarial+parasites%2C+and+one+analog+demonstrated+lower+membrane+permeability%2C+which+is+potentially+advantageous+for+the+reduction+of+the+neurotoxic+side+effects.+As+part+of+this+work%2C+we+also+report+the+first+SF5-containing+quinoline+heterocycles+and+the+first+ortho+SF5+aniline.&rft.date=2010-09-20&rft.type=University+of+Pittsburgh+ETD&rft.type=PeerReviewed&rft.format=application%2Fpdf&rft.language=en&rft.identifier=http%3A%2F%2Fd-scholarship-dev.library.pitt.edu%2F7773%2F1%2FTingtingMo_MSETD2010_2.pdf&rft.identifier=++Mo%2C+Tingting++(2010)+Synthesis+of+Pentafluorosulfanyl+Analogs+of+Mefloquine.++Master's+Thesis%2C+University+of+Pittsburgh.++++(Unpublished)++